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Hydrochloric Acid → 3-(3-Amino-4-trifluoromethoxyphenyl)5,5-dimethyl-1-pyridin-4-ylmethylimidazolidine-2,4-dione

HRID 2356932
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Reaktionsgleichung

Reaktionsgleichung von HRID 2356932
[CH3:1][C:2]1([CH3:30])[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=2)[C:5](=[O:14])[N:4]([C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]([F:25])([F:24])[F:23])=[C:17]([N+:26]([O-])=O)[CH:16]=2)[C:3]1=[O:29].Cl>O.[Zn]>[NH2:26][C:17]1[CH:16]=[C:15]([N:4]2[C:3](=[O:29])[C:2]([CH3:30])([CH3:1])[N:6]([CH2:7][C:8]3[CH:13]=[CH:12][N:11]=[CH:10][CH:9]=3)[C:5]2=[O:14])[CH:20]=[CH:19][C:18]=1[O:21][C:22]([F:23])([F:24])[F:25]
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Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 23110306HCID 23110306, Verbindung

Produkt 1

HCID 231103083-(3-Amino-4-trifluoromethoxyphenyl)5,5-dimethyl-1-pyridin-4-ylmethylimidazolidine-2,4-dioneAusbeute 57,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

8.8 g (20.7 mmol ) 5,5-dimethyl-3-(3-nitro-4-trifluormethoxy-phenyl)-1-pyridin-4-ylmethyl-imidazolidine-2,4-dione were dissolved in 200 ml semi-conc. hydrochloric acid. 30 g zinc dust were added in portions and the resulting mixture was refluxed for 1 h, cooled to RT, diluted with 100 ml water and extracted with ethyl acetate. The aqueous phase was made alkaline with saturated sodium hydroxide solution and extracted with methylene chloride. Separating zinc salts were removed by filtration over cellite. Evaporation of the combined organic phases and flash chromoatography of the residue (Silica gel, methylene chloride:methanol=95:5) gave 4.7 g of the desired product.

Aufarbeitung

  1. temperaturethe resulting mixture was refluxed for 1 h
  2. extractionextracted with ethyl acetate
  3. extractionextracted with methylene chloride
  4. customSeparating zinc salts were removed by filtration over cellite
  5. customEvaporation of the combined organic phases and flash chromoatography of the residue (Silica gel, methylene chloride:methanol=95:5)

Quellen und Nachweise

ORD-Eintrag
ord-7f2072eb7b7742a695baf08a0bdc93a4
Quelldatensatz
uspto-grants-2010_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07759379B2

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